Editing Chloroform (section)

==Uses==
In terms of scale, the most important reaction of chloroform is with [[hydrogen fluoride]] to give [[monochlorodifluoromethane]] (HCFC-22), a precursor in the production of polytetrafluoroethylene ([[Teflon]]) and other fluoropolymers:<ref name="Ullmann" />
:{{chem2|CHCl3 + 2 HF → CHClF2 + 2 HCl}}
The reaction is conducted in the presence of a [[Catalysis|catalytic]] amount of [[Antimony trifluoride#Applications|mixed antimony halides]]. Chlorodifluoromethane is then converted to [[tetrafluoroethylene]], the main precursor of [[Teflon]].<ref>{{Cite web|title=Chlorodifluoromethane {{!}} chemical compound|url=https://www.britannica.com/science/chlorodifluoromethane|access-date=2021-09-08|website=Encyclopedia Britannica|language=en|archive-date=17 July 2021|archive-url=https://web.archive.org/web/20210717174046/https://www.britannica.com/science/chlorodifluoromethane|url-status=live}}</ref>

===Solvent===
The [[hydrogen]] attached to [[carbon]] in chloroform participates in hydrogen bonding,<ref>{{cite journal|last1=Wiley |first1=G. R. |last2=Miller |first2=S. I. |doi=10.1021/ja00765a001|title=Thermodynamic parameters for hydrogen bonding of chloroform with Lewis bases in cyclohexane. Proton magnetic resonance study|year=1972|journal=Journal of the American Chemical Society|volume=94|issue=10|pages=3287–3293}}</ref><ref>{{cite journal|pmid=18855462|year=2008|last1=Kwak|first1=K.|last2=Rosenfeld|first2=D. E.|last3=Chung|first3=J. K.|last4=Fayer|first4=M. D.|title=Solute-solvent complex switching dynamics of chloroform between acetone and dimethylsulfoxide-two-dimensional IR chemical exchange spectroscopy|volume=112|issue=44|pages=13906–13915|doi=10.1021/jp806035w|pmc=2646412|journal=The Journal of Physical Chemistry B}}</ref> making it a good solvent for many materials. 

Worldwide, chloroform is also used in pesticide formulations, as a [[solvent]] for [[lipids]], [[rubber]], [[alkaloid]]s, [[wax]]es, [[gutta-percha]], and [[resin]]s, as a cleaning agent, as a grain [[fumigant]], in [[fire extinguishers]], and in the rubber industry.<ref name="cicad">{{citation | title=Chloroform | series=[[CICAD]] | volume=58 | publisher=[[World Health Organization]] | year=2004 | url=https://www.who.int/ipcs/publications/cicad/en/cicad58.pdf | url-status=live | archive-url=https://web.archive.org/web/20200731202031/https://www.who.int/ipcs/publications/cicad/en/cicad58.pdf | archive-date=31 July 2020}}</ref><ref name="pth">{{cite encyclopedia| editor1-last=Leikin |editor1-first=Jerrold B. | editor2-last=Paloucek |editor2-first=Frank P. | title=Chloroform | encyclopedia=Poisoning and Toxicology Handbook | edition=4th | publisher=Informa | year=2008 | page=774}}</ref> [[deuterated chloroform|{{chem2|CDCl3}}]] is a common solvent used in [[NMR spectroscopy]].<ref>{{cite journal|doi=10.1021/om100106e|title=NMR Chemical Shifts of Trace Impurities: Common Laboratory Solvents, Organics, and Gases in Deuterated Solvents Relevant to the Organometallic Chemist|journal=Organometallics|volume=29|issue=9|pages=2176–2179|year=2010|last1=Fulmer|first1=Gregory R.|last2=Miller|first2=Alexander J. M.|last3=Sherden|first3=Nathaniel H.|last4=Gottlieb|first4=Hugo E.|last5=Nudelman|first5=Abraham|last6=Stoltz|first6=Brian M.|last7=Bercaw|first7=John E.|last8=Goldberg|first8=Karen I.|s2cid=2755004 |url=https://authors.library.caltech.edu/18475/2/om100106e_si_001.pdf}}</ref>

===Refrigerant===
Chloroform is used as a precursor to make R-22 (chlorodifluoromethane). This is done by reacting it with a solution of [[hydrofluoric acid]] (HF) which fluorinates the {{chem2|CHCl3}} molecule and releases hydrochloric acid as a byproduct.<ref>{{cite web | url=https://www.ebi.ac.uk/chebi/es/searchId.do?printerFriendlyView=true&locale=null&chebiId=35255&viewTermLineage=null&structureView=&|title=Chloroform (CHEBI:35255)}}</ref> Before the [[Montreal Protocol]] was enforced, most of the chloroform produced in the United States was used in the production of [[chlorodifluoromethane]]. However, its production remains high, as it is a key precursor of PTFE.<ref>{{cite web|url=https://www.atsdr.cdc.gov/ToxProfiles/tp6-c4.pdf|title=Production, import/export, use, and disposal|access-date=5 April 2023|website=atsdr.cdc.gov}}</ref> 

Although chloroform has properties such as a low boiling point, and a low global warming potential of only 31 (compared to the 1760 of R-22), which are appealing properties for a refrigerant, there is little information to suggest that it has seen widespread use as a refrigerant in any consumer products.<ref>{{cite encyclopedia| title=Chloroform as a pollutant |encyclopedia=The Encyclopedia of World Problems | url=http://encyclopedia.uia.org/en/problem/chloroform-pollutant#:~:text=Most%20chloroform%20is%20manufactured%20to,spot%20removers%2C%20and%20various%20solvents}}</ref>

===Lewis acid===
In solvents such as {{chem2|CCl4}} and alkanes, chloroform hydrogen bonds to a variety of Lewis bases. {{chem2|HCCl3}} is classified as a [[HSAB|hard acid]], and the [[ECW model]] lists its acid parameters as E<sub>A</sub> = 1.56 and C<sub>A</sub> = 0.44.

===Reagent===
As a [[reagent]], chloroform serves as a source of the [[dichlorocarbene]] intermediate {{chem2|CCl2}}.<ref>{{cite encyclopedia|last1=Srebnik |first1=M. |last2=Laloë |first2=E. |date=2001 |encyclopedia=Encyclopedia of Reagents for Organic Synthesis |publisher=Wiley |doi=10.1002/047084289X.rc105|chapter=Chloroform |isbn=978-0-471-93623-7 }}</ref> It reacts with aqueous [[sodium hydroxide]], usually in the presence of a [[phase transfer catalyst]], to produce [[dichlorocarbene]], {{chem2|CCl2}}.<ref>{{OrgSynth|last1=Vogel |first1=E. |last2=Klug |first2=W. |last3=Breuer |first3=A.|title = 1,6-Methano[10]annulene|collvol = 6|collvolpages = 731|year = 1988|prep = cv6p0731}}</ref><ref>{{OrgSynth|last1 = Gokel |first1=G. W. |last2=Widera|first2= R. P. |last3=Weber |first3=W. P.|title = Phase-Transfer Hofmann Carbylamine Reaction: ''tert''-Butyl Isocyanide|collvol = 6|collvolpages = 232|year = 1988|prep = cv6p0232}}</ref> This reagent effects ortho-formylation of activated [[aromatic rings]], such as [[phenols]], producing aryl [[aldehyde]]s in a reaction known as the [[Reimer–Tiemann reaction]]. Alternatively, the [[carbene]] can be trapped by an [[alkene]] to form a [[cyclopropane]] derivative. In the [[Kharasch addition]], chloroform forms the {{chem2|•CHCl2}} free radical which adds to alkenes.{{citation needed|date=November 2020}}

===Anaesthetic===
[[File:Chickamauga 2009, Chloroform.jpg|thumb|Antique bottles of chloroform]]
Chloroform is a powerful [[general anesthetic]], [[euphoriant]], [[anxiolytic]], and [[sedative]] when inhaled or ingested. The [[anaesthetic]] qualities of chloroform were first described in 1842 in a thesis by [[Robert Mortimer Glover]], which won the Gold Medal of the [[Harveian Society]] for that year.<ref name="Chloroform History">{{cite journal |last1=Perkins-McVey |first1=Matthew |title="A new order of poisonous substances": revisiting Robert M. Glover's dissertation on the physiological effects of bromine, chlorine, and iodine compounds |journal=Naunyn-Schmiedeberg's Archives of Pharmacology |date=10 November 2023 |volume=397 |issue=5 |pages=3343–3350 |doi=10.1007/s00210-023-02820-y |url=https://www.researchgate.net/publication/375556103 |access-date=27 January 2024|doi-access=free |pmid=37947840 }}</ref><ref>{{cite journal |last1=Glover |first1=Robert M. |title=On the Physiological and Medicinal Properties of Bromine and Its Compounds; Also on the Analogies between the Physiological and Medicinal Properties of These Bodies, and Those of Chlorine and Iodine, with Their Correspondent Compounds; Being the Harveian Prize Essay for 1842. |journal=Edinburgh Medical and Surgical Journal |date=1 October 1842 |volume=58 |issue=153 |pages=335–364 |pmid=30330609 |pmc=5789197 }}</ref> Glover also undertook practical experiments on dogs to prove his theories, refined his theories, and presented them in his doctoral thesis at the [[University of Edinburgh]] in the summer of 1847, identifying anaesthetizing halogenous compounds as a "new order of poisonous substances".<ref name="Chloroform History" />

The Scottish [[obstetrics|obstetrician]] [[James Young Simpson]] was one of those examiners required to read the thesis, but later claimed to have never read it and to have come to his own conclusions independently.<ref name="Chloroform History" /> Perkins-McVey, among others, have raised doubts about the credibility of Simpson's claim, noting that Simpson's publications on the subject in 1847 explicitly echo Glover's and, being one of the thesis examiners, Simpson was likely aware of the content of Glover's study, even if he skirted his duties as an examiner.<ref name="Chloroform History" /> In 1847 and 1848, Glover would pen a series of heated letters accusing Simpson of stealing his discovery, which had already earned Simpson considerable notoriety.<ref name="Chloroform History" /> Whatever the source of his inspiration, on 4 November 1847, Simpson argued that he had discovered the anaesthetic qualities of chloroform in humans. He and two colleagues entertained themselves by trying the effects of various substances, and thus revealed the potential for chloroform in medical procedures.<ref name="Gordon2002">{{cite book|last=Gordon|first=H. Laing|title=Sir James Young Simpson and Chloroform (1811–1870)|url=https://books.google.com/books?id=pYer05UwKBYC&pg=PA106|date=November 2002|publisher=Minerva Group|isbn=978-1-4102-0291-8|pages=106–109|access-date=5 January 2016|archive-date=6 May 2016|archive-url=https://web.archive.org/web/20160506214333/https://books.google.com/books?id=pYer05UwKBYC&pg=PA106|url-status=live}}</ref>
[[File:James Young Simpson chloroform.png|thumb|An illustration depicting James Young Simpson and his friends found unconscious.]]
A few days later, during the course of a dental procedure in [[Edinburgh]], [[Francis Brodie Imlach]] became the first person to use chloroform on a patient in a clinical context.<ref>{{cite web |last=Dingwall |date=April 2004 |url=http://historyofdentistry.co.uk/index_htm_files/2004Apr2.pdf |title=A pioneering history: dentistry and the Royal College of Surgeons of Edinburgh |website=historyofdentistry.co.uk  |archive-url=https://web.archive.org/web/20130201191323/http://historyofdentistry.co.uk/index_htm_files/2004Apr2.pdf |archive-date=1 February 2013}}</ref>

In May 1848, [[Robert Halliday Gunning]] made a presentation to the Medico-Chirurgical Society of Edinburgh following a series of laboratory [[Domestic rabbit#Experimentation|experiments on rabbits]] that confirmed Glover's findings and also refuted Simpson's claims of originality. The laboratory experiments that proved the dangers of chloroform were largely ignored.<ref>{{cite journal |url=https://www.royalsoced.org.uk/cms/files/research_awards/prizes/prize_lists/gunning_victoria_history.pdf |title=Robert Halliday Gunning and the Victoria Jubilee Prizes |year=2003 |access-date=2016-08-18  |archive-url=https://web.archive.org/web/20160822105053/https://www.royalsoced.org.uk/cms/files/research_awards/prizes/prize_lists/gunning_victoria_history.pdf |archive-date=22 August 2016 |doi=10.1177/003693300304800209 |last1=Baillie |first1=T. W. |journal=Scottish Medical Journal |volume=48 |issue=2 |pages=54–57 |pmid=12774598 |s2cid=10998512 }}</ref>

The use of chloroform during [[surgery]] expanded rapidly in Europe; for instance in the 1850s chloroform was used by the physician [[John Snow]] during the births of [[Queen Victoria]]'s last two children [[Prince Leopold, Duke of Albany|Leopold]] and [[Princess Beatrice of the United Kingdom|Beatrice]].<ref>{{cite web |url=http://www.ph.ucla.edu/epi/snow/victoria.html |title=Anesthesia and Queen Victoria |website=ph.ucla.edu |access-date=13 August 2012 |url-status=live |archive-url=https://web.archive.org/web/20120716005223/http://www.ph.ucla.edu/epi/snow/victoria.html |archive-date=16 July 2012}}</ref> In the United States, chloroform began to replace [[Diethyl ether|ether]] as an anesthetic at the beginning of the 20th century;<ref name="Chloroform History in U.S.">{{cite journal |last1=Wawersik |first1=J |title=[History of chloroform anesthesia]. |journal=Anaesthesiologie und Reanimation |date=1997 |volume=22 |issue=6 |pages=144-52 |pmid=9487785 |url=https://pubmed.ncbi.nlm.nih.gov/9487785/}}</ref> it was abandoned in favor of ether on discovery of its toxicity, especially its tendency to cause fatal [[cardiac arrhythmia|cardiac arrhythmias]] analogous to what is now termed "[[Intoxicative inhalant#Sudden sniffing death syndrome|sudden sniffer's death]]". Some people used chloroform as a recreational drug or to attempt suicide.<ref>{{cite journal|last=Martin|first=William|title=A Case of Chloroform Poisoning; Recovery|journal=British Medical Journal|date=3 July 1886|volume=2|issue=1331|pages=16–17|pmc=2257365|doi=10.1136/bmj.2.1331.16-a|pmid=20751619}}</ref> One possible mechanism of action of chloroform is that it increases the movement of [[potassium]] ions through certain types of [[potassium channel]]s in [[nerve cells]].<ref>{{Cite journal|last1 = Patel|first1 = Amanda J.|last2 = Honoré|first2 = Eric|last3 = Lesage|first3 = Florian|last4 = Fink|first4 = Michel|last5 = Romey|first5 = Georges|last6 = Lazdunski|first6 = Michel|date = May 1999|title = Inhalational anesthetics activate two-pore-domain background K<sup>+</sup> channels|journal = Nature Neuroscience|volume = 2|pages = 422–426|doi = 10.1038/8084|pmid = 10321245|issue = 5|s2cid = 23092576}}</ref> Chloroform could also be mixed with other anesthetic agents such as ether to make C.E. mixture,<ref name="Chloroform & Ether">{{cite journal |last1=von Hintzenstern |first1=U. |last2=Schwarz |first2=W. |title=Frühe Erlanger Beiträge zur Theorie und Praxis der Ather- und Chloroformnnarkose |journal=Der Anaesthesist |date=1 February 1996 |volume=45 |issue=2 |pages=131–139 |doi=10.1007/s001010050247 |pmid=8720885 |url=https://pubmed.ncbi.nlm.nih.gov/8720885/ |access-date=17 March 2025 |trans-title=Early contributions from Erlangen to the theory and practice of ether and chloroform anesthesia. 1. Heyfelder's clinical trial with ether and chloroform |language=de}}</ref> or ether and [[Ethanol|alcohol]] to make [[A.C.E. mixture]].<ref name="Alcohol, Chloroform & Ether">{{cite journal |title=An Experience with the New Anæsthetic-Chloroform, Ether and Absolute Alcohol. |journal=The Independent practitioner |date=February 1883 |volume=4 |issue=2 |pages=97-100 |pmid=37826124 |url=https://pubmed.ncbi.nlm.nih.gov/37826124/ |access-date=17 March 2025 |language=English |pmc=10072673}}</ref><ref name="ACE Mixture">{{cite journal |last1=Shah |first1=Shrey P. |last2=Bause |first2=George S. |title=From ACE to ACENO: How America's Munson added Harley's British mixture to nitrous oxide |journal=Journal of Anesthesia History |date=September 2020 |volume=6 |issue=3 |pages=168–169 |doi=10.1016/j.janh.2020.07.006 |pmid=32921491 |url=https://pubmed.ncbi.nlm.nih.gov/32921491/ |access-date=17 March 2025}}</ref> 

In 1848, Hannah Greener, a 15-year-old girl who was having an infected toenail removed, died after being given the anaesthetic.<ref>{{cite journal|title=An Unexplained Death: Hannah Greener and Chloroform |last1=Knight |first1=Paul R. III |last2=Bacon |first2=Douglas R. |s2cid=12865865 | year=2002 |volume = 96 |issue = 5 |journal=Anesthesiology|doi=10.1097/00000542-200205000-00030|pages=1250–1253|pmid=11981167|doi-access=free }}</ref> Her autopsy establishing the cause of death was undertaken by [[John Fife (surgeon)|John Fife]] assisted by [[Robert Mortimer Glover]].<ref name=pdf1/> A number of physically fit patients died after inhaling it. In 1848, however, John Snow developed an inhaler that regulated the dosage and so successfully reduced the number of deaths.<ref>{{cite book|last1 = Snow|first1 = John|year = 1858|title = On Chloroform and Other Anaesthetics and Their Action and Administration|pages = 82–85|url = https://archive.org/stream/onchloroformothe1858snow#page/82/mode/2up/search/inhaler|url-status = live|archive-url = http://archive.wikiwix.com/cache/20151123021418/https://archive.org/stream/onchloroformothe1858snow#page/82/mode/2up/search/inhaler|archive-date = 23 November 2015|publisher = London : John Churchill}}</ref>

The opponents and supporters of chloroform disagreed on the question of whether the medical complications were due to respiratory disturbance or whether chloroform had a specific effect on the heart. Between 1864 and 1910, numerous commissions in Britain studied chloroform but failed to come to any clear conclusions. It was only in 1911 that Levy proved in experiments with animals that chloroform can cause ventricular fibrillation.<ref name="Chloroform ventricular fibrillation">{{cite journal |last1=Hutcheon |first1=D. E. |title=SUSCEPTIBILITY TO VENTRICULAR FIBRILLATION DURING CHLOROFORM AND CYCLOPROPANE ANAESTHESIA |journal=British Journal of Pharmacology and Chemotherapy |date=March 1951 |volume=6 |issue=1 |pages=31–34 |doi=10.1111/j.1476-5381.1951.tb00617.x |pmid=14821299 |url=https://pubmed.ncbi.nlm.nih.gov/37826124/ |access-date=17 March 2025 |language=English |pmc=1509204}}</ref> Despite this, between 1865 and 1920, chloroform was used in 80 to 95% of all narcoses performed in the UK and German-speaking countries. In Germany, comprehensive surveys of the fatality rate during anaesthesia were made by Gurlt between 1890 and 1897.<ref name="Chloroform History in U.S." /> At the same time in the UK the medical journal ''[[The Lancet]]'' carried out a questionnaire survey<ref>{{Cite journal |last=Anonymous. |date=1890 |title=The Lancet Inquiry into the Mortality Under Anaesthetics. |journal=Lancet |volume=145 |issue=3472 |pages=612–13}}</ref> and compiled a report detailing numerous adverse reactions to anesthetics, including chloroform.<ref>{{Cite journal |last=Anonymous. |date=1893 |title=Report of The Lancet Commission appointed to investigate the subject of the administration of chloroform and other anesthetics from a clinical standpoint. |journal=Lancet |volume=141 |issue=3629 |pages=629–38}}</ref> In 1934, Killian gathered all the statistics compiled until then and found that the chances of suffering fatal complications under ether were between 1:14,000 and 1:28,000, whereas with chloroform the chances were between 1:3,000 and 1:6,000.<ref name="Chloroform History in U.S." /> The rise of gas anaesthesia using [[nitrous oxide]], improved equipment for administering anesthetics, and the discovery of [[hexobarbital]] in 1932 led to the gradual decline of chloroform narcosis.<ref>{{cite journal | pmid = 9487785 | volume=22 | issue=6 | title=History of chloroform anesthesia | year=1997 | journal=Anesthesiology and Reanimation | pages=144–152 | last= Wawersik |first=J.}}</ref>

The latest reported anaesthetic use of chloroform in the Western world dates to 1987, when the last doctor who used it retired, about 140 years after its first use.<ref>{{cite book|last=Stratmann|first=Linda|date=2003|title=Chloroform: The Quest for Oblivion|location=Stroud|publisher=Sutton Publishing|isbn=978-0-7524-9931-4}}</ref>

=== Criminal use ===
[[File:Damsels in distress chloroformed.jpg|thumb|[[Damsel in distress|Damsels in distress]] being knocked out with chloroform in various media]]
Chloroform has been used by criminals to knock out, daze, or murder victims. Joseph Harris was charged in 1894 with using chloroform to rob people.<ref>{{cite news|url=https://news.google.com/newspapers?id=Ec1VAAAAIBAJ&pg=2904,2720400&dq=chloroform+knockout&hl=en|title=Knock-out and Chloroform|newspaper=[[The Philadelphia Record]]|date=9 February 1894|access-date=31 March 2011|archive-date=20 January 2022|archive-url=https://web.archive.org/web/20220120054325/https://news.google.com/newspapers?id=Ec1VAAAAIBAJ&pg=2904,2720400&dq=chloroform+knockout&hl=en|url-status=live}}</ref> [[Serial killer]] [[H. H. Holmes]] used chloroform overdoses to kill his female victims. In September 1900, chloroform was implicated in the murder of the U.S. businessman [[William Marsh Rice]]. Chloroform was deemed a factor in the alleged murder of a woman in 1991, when she was asphyxiated while asleep.<ref>{{cite news|url=https://news.google.com/newspapers?id=I91HAAAAIBAJ&pg=2367,1007950&dq=chloroform+knockout&hl=en|title=Chloroform case retrial underway|date=7 July 1993|access-date=31 March 2011|newspaper=[[Record-Journal]]|archive-date=6 November 2021|archive-url=https://web.archive.org/web/20211106203133/https://news.google.com/newspapers?id=I91HAAAAIBAJ&pg=2367%2C1007950&dq=chloroform+knockout&hl=en|url-status=live}}</ref> In 2002, 13-year-old [[Murder of Kacie Woody|Kacie Woody]] was sedated with chloroform when she was abducted by David Fuller and during the time that he had her, before he shot and killed her.<ref>{{Cite web|url=https://www.arkansasonline.com/news/2003/dec/17/not-forgotten/|title=But not forgotten|last=Cathy Frye - [[Arkansas Democrat-Gazette]]|date=2003-12-17|website=www.arkansasonline.com|access-date=2021-12-07|archive-date=7 December 2021|archive-url=https://web.archive.org/web/20211207200713/https://www.arkansasonline.com/news/2003/dec/17/not-forgotten/|url-status=live}}</ref> In a 2007 plea bargain, a man confessed to using [[Electroshock weapon|stun guns]] and chloroform to sexually assault minors.<ref>{{cite news|url=https://www.usatoday.com/news/nation/2007-11-06-chloroform-rapes_N.htm|title=Man admits to raping friends' daughters|date=6 November 2007|access-date=31 March 2011|newspaper=[[USA Today]]|url-status=live|archive-url=https://web.archive.org/web/20110429075437/http://www.usatoday.com/news/nation/2007-11-06-chloroform-rapes_N.htm|archive-date=29 April 2011}}</ref>

The use of chloroform as an [[incapacitating agent]] has become widely recognized, bordering on [[cliché]], through the adoption by [[crime fiction]] authors of plots involving criminals' use of chloroform-soaked rags to render victims unconscious. However, it is nearly impossible to incapacitate someone using chloroform in this way.<ref name="Anaesthesia">{{cite journal|last=Payne|first=J. P.|s2cid=1718276|date=July 1998|title=The criminal use of chloroform|journal=[[Anaesthesia (journal)|Anaesthesia]]|volume=53|issue=7|pages=685–690|doi=10.1046/j.1365-2044.1998.528-az0572.x|pmid=9771177|doi-access=free}}</ref> It takes at least five minutes of inhalation of chloroform to render a person unconscious. Most criminal cases involving chloroform involve co-administration of another drug, such as [[ethanol|alcohol]] or [[diazepam]], or the victim being complicit in its administration. After a person has lost consciousness owing to chloroform inhalation, a continuous volume must be administered, and the chin must be supported to keep the tongue from obstructing the airway, a difficult procedure, typically requiring the skills of an [[anesthesiologist]]. In 1865, as a direct result of the criminal reputation chloroform had gained, the medical journal ''[[The Lancet]]'' offered a "permanent scientific reputation" to anyone who could demonstrate "instantaneous insensibility", i.e. loss of consciousness, using chloroform.<ref>{{cite journal|title=Medical Annotation: Chloroform amongst Thieves |journal=[[The Lancet]] |date=1865 |volume=2 |issue=2200 |pages=490–491|doi=10.1016/s0140-6736(02)58434-8}}</ref>